Chicago Summer Festivals in 2024 Summer Festivals (June to September) 01 Jun 01 Jun - 02 Jun Beyond Wonderland Chicago 2024 June 1, 2024 at 02:00 PM - June 2, 2024 at 11:00 PM Huntington Bank Pavilion (Northerly Island) Music Festival 06 Jun 06 Jun - 09 Jun Chicago Blues Festival 2024 June 6, 2024 - June 9, 2024 Millennium Park Music Festival 21 Jun 21 Jun - 23 Jun Motoblot 2024 June 21, 2024 - June 23, 2024 Cobra Lounge Car & Auto 28 Jun 28 Jun Sangria Fest on the Beach – Sangria Tasting at North Ave. Beach June 28, 2024 at 06:00 PM - 09:00 PM Shore Club Chicago Wine Festival 06 Jul 06 Jul - 07 Jul NASCAR Chicago Street Race 2024 July 6, 2024 at 09:00 AM - July 7, 2024 Grant Park Car & Auto 11 Jul 11 Jul - 14 Jul Windy City Smokeout 2024 July 11, 2024 - July 14, 2024 United Center Music Festival 19 Jul 19 Jul - 21 Jul Pitchfork Music Festival 2024 July 19, 2024 - July 21, 2024 Union Park Music Festival 20 Jul 20 Jul - 21 Jul Chicago Food Truck Festival – Summer 2024 July 20, 2024 at 11:00 AM - July 21, 2024 at 07:00 PM 2300 S. Indiana Ave. (South Loop) Food Festival 01 Aug 01 Aug - 04 Aug Lollapalooza Chicago 2024 August 1, 2024 - August 4, 2024 Grant Park Music Festival 30 Aug 30 Aug - 01 Sep North Coast Music Festival 2024 August 30, 2024 - September 1, 2024 SeatGeek Stadium Music Festival 06 Sep 06 Sep - 08 Sep Taste of Chicago 2024 September 6, 2024 - September 8, 2024 - Food Festival 06 Sep 06 Sep Sangria Fest on the Beach – Sangria Tasting at North Ave. Beach September 6, 2024 at 06:00 PM - 09:00 PM Shore Club Chicago Wine Festival 07 Sep 07 Sep - 08 Sep Printers Row Lit Fest 2024 September 7, 2024 at 10:00 AM - September 8, 2024 at 06:00 PM Printers Row Literary Festival 11 Sep 11 Sep - 15 Sep Chicago Underground Film Festival 2024 September 11, 2024 - September 15, 2024 - Film Festival 20 Sep 20 Sep - 22 Sep Riot Fest 2024 September 20, 2024 - September 22, 2024 Douglass Park Music Festival